Phosphorus oxychloride → methyl 2-chloro-5-(4-methoxybutyl)-1-phenyl-1H-imidazole-4-carboxylate
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10](=O)[NH:9][C:8]=1[C:19]([O:21][CH3:22])=[O:20].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:10]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[C:8]([C:19]([O:21][CH3:22])=[O:20])[N:9]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
Methyl 5-(4-methoxybutyl)-2-oxo-1-phenyl-2,3-dihydro-1H-imidazole-4-carboxylate (1.50 g) was dissolved in phosphorus oxychloride (18 ml) and the mixture was stirred at 100° C. for 10 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was diluted with saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object product (454 mg).
Workup
- temperatureAfter cooling to room temperature
- concentrationthe reaction mixture was concentrated under reduced pressure
- additionThe residue was diluted with saturated aqueous sodium hydrogen carbonate solution
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- washa fraction eluted with ethyl acetate-hexane (10:90-100:0)
- concentrationwas concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-291888bee94d4f83acb74eb4fb7ab732
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466282B2
Reaction notes
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